Synthesis, characterization and in vitro Antiamoebic Activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones and their Palladium (II) and Ruthenium (II) Complexes

• Published in: European journal of medicinal chemistry 2004-05, Vol.39 (5), p.459-465
• Main Authors: Singh, Shailendra, Bharti, Neelam, Naqvi, Fehmida, Azam, Amir
• Format: Article
• Language: English
• Subjects: 5-Nitrothiophene-2-carboxaldehyde; Amebicides - chemical synthesis; Amebicides - chemistry; Amebicides - pharmacology; Animals; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiparasitic agents; Biological and medical sciences; Entamoeba histolytica - drug effects; In vitro antiamoebic activity; Inhibitory Concentration 50; Medical sciences; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Organometallic Compounds - pharmacology; Palladium (II) complexes; Palladium - chemistry; Parasitic Sensitivity Tests; Pharmacology. Drug treatments; Ruthenium (II) complexes; Ruthenium - chemistry; Spectrum Analysis - methods; Thiosemicarbazones; Thiosemicarbazones - chemical synthesis; Thiosemicarbazones - chemistry; Thiosemicarbazones - pharmacology
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2004.02.003

Synthesis of new Palladium(II) and Ruthenium(II) complexes of the type, [Pd(L)Cl 2] and [Ru(η 4-C 8H 12)(L)Cl 2] {where, L = thiosemicarbazones derived from 5-nitrothiophene-2-carboxaldehyde and cycloalkylaminothiocarbonyl hydrazines} have been isolated by the reaction of [Pd(DMSO) 2Cl 2] and [Ru(η 4-C 8H 12)(CH 3CN) 2Cl 2] with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones. The spectral data revealed that the thiosemicarbazones act as bidentate ligands, making use of thionic sulphur and the azomethine nitrogen atom for coordination to the central metal ion. Microdilution method was used for the assessment of antiamoebic activity of all the compounds against HK-9 strain of Entamoeba histolytica. Among all the thiosemicarbazones, 5-NT-4-BPTSCN ( 3) showed significant antiamoebic activity (IC 50 – 2.56 μM). Enhancement of antiamoebic activity resulted by introducing palladium and ruthenium metals in the thiosemicarbazone moiety. All the Pd(II) and Ru(II) complexes of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones were found more active then their respective ligands. The complexes 1a-4a, 1b and 3b showed antiamoebic activity.